Sodium Bicarbonate → 3-Oxa-8-azabicyclo[3.2.1]oct-8-yl(8-(1,3-oxazol-5-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)methanone

HRID 931049노트

반응식

HRID 931049 반응식
[O:1]1[C:5]([C:6]2[C:7]3[N:8]([C:16]([C:19]([OH:21])=O)=[CH:17][N:18]=3)[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=2)=[CH:4][N:3]=[CH:2]1.F[P-](F)(F)(F)(F)F.C(C(=NO[C+](N(C)C)N1CCOCC1)C(OCC)=O)#N.Cl.[CH:50]12[NH:57][CH:54]([CH2:55][CH2:56]1)[CH2:53][O:52][CH2:51]2.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(N(CC)CC)C>[CH:54]12[N:57]([C:19]([C:16]3[N:8]4[CH:9]=[C:10]([C:12]([F:13])([F:14])[F:15])[CH:11]=[C:6]([C:5]5[O:1][CH:2]=[N:3][CH:4]=5)[C:7]4=[N:18][CH:17]=3)=[O:21])[CH:50]([CH2:56][CH2:55]1)[CH2:51][O:52][CH2:53]2

참가 물질

7

반응물 4

HCID 516892Sodium BicarbonateHCID 534011293-Oxa-8-azabicyclo(3.2.1)octane hydrochlorideHCID 1183789628-(1,3-Oxazol-5-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acidHCID 178472143HCID 178472143, 화합물

생성물 1

HCID 1183790013-Oxa-8-azabicyclo[3.2.1]oct-8-yl(8-(1,3-oxazol-5-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)methanone수율 98.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

To a mixture of 8-(1,3-oxazol-5-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid (80 g), triethylamine (113 mL) and DMF (2000 mL) were added (1-cyano-2-ethoxy-2-oxoethylideneaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate (127 g) and 3-oxa-8-azabicyclo[3.2.1]octane hydrochloride (42.3 g) at 0° C., and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added saturated aqueous sodium bicarbonate solution at 0° C. The obtained solid was collected by filtration, and washed with saturated aqueous sodium bicarbonate solution, water, ethanol and methyl tert-butyl ether to give the title compound (104 g).

후처리

  1. filtrationThe obtained solid was collected by filtration
  2. washwashed with saturated aqueous sodium bicarbonate solution, water, ethanol and methyl tert-butyl ether

출처 및 근거

ORD 기록
ord-13d0acf4265a4864b296c714245693bb
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296746B2

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